


Inside and Out

by ImogenPortchester



Category: Supernatural
Genre: Coming Out, Crossdressing, Dean in Makeup, Dean in Panties, F/M, Gen, Gender Dysphoria, Gender Identity, Hell Trauma, Hurt Dean Winchester, Hurt/Comfort, Post-Traumatic Stress Disorder - PTSD, Sad Dean Winchester, Support Group
Language: English
Status: Completed
Published: 2016-01-15
Updated: 2018-04-02
Packaged: 2018-05-14 01:52:28
Rating: Mature
Warnings: No Archive Warnings Apply
Chapters: 13
Words: 9,732
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/5725315
Author URL: https://archiveofourown.org/users/ImogenPortchester/pseuds/ImogenPortchester
Summary: <blockquote class="userstuff">
              <p>For as long as he can remember Dean has never felt comfortable in his own body.</p><p>--<br/>Chapter 13 is new as of April 2, 2018!</p>
            </blockquote>





	1. I

**Author's Note:**

> I will probably keep adding to this periodically, but for now I'm posting it as complete. Each of these little vignettes can probably stand on its own, but they make up a larger picture which is this "story".
> 
> This is a subject that is near and dear to my heart, so I really hope that I did it justice. I really hope you guys like this!
> 
> This is un-beta'd so all mistakes are my own.

Dean keeps a pack of Pall Mall Menthols at the back of his sock and underwear drawer, where he also keeps the little bit of makeup he owns. Sam, who’s a disgusting human being that never does laundry, needs to borrow a pair of Dean’s socks because all of his own are dirty. On a Friday morning while Dean is still asleep, Sam creeps into his brother’s bedroom and opens up the top dresser drawer and fishes around in the dark for a pair of socks. His hand brushes against the hard plastic of a small eye shadow palette and he continues on his quest for socks, not realizing in the dark what it is. He grabs a pair of socks and exits the room as quietly as possible, all the while not noticing that Dean lay awake, staring at Sam’s shadowed movements. 

When the door clicks shut Dean releases the breath he had been holding for what felt like an eternity. He isn’t able to fall back asleep.


	2. II

Dean leans against the hood of the Impala, waiting as Sam finishes interviewing the pretty brunette college student after Dean had successfully executed his bad cop routine. He pulls a cigarette to his lips and sucks, holding the hot smoke in his mouth before breathing it in. He exhales through his nose and shifts uncomfortably, the tag of his new lace thong chafing him in a way he hadn’t anticipated. He had gotten dressed too quickly this morning and he and Sam were already on their way to interview witnesses before the problem reared its ugly head. When he’s smoked the cigarette down to butt, he flicks it to the ground and crushes it under his shoe.

He should quit, he knows. Sam doesn’t like his smoking and is sure to let Dean know how he feels quite often. But it’s a habit Dean’s had since high school and he likes it. And anyway, there are plenty of worse habits he could have picked up over the years. A cigarette is something to calm his nerves before or after a stressful event. Like hunting, like sex, like…

Sam exits the building and gives Dean a thumbs up as he makes his way to the car. Dean climbs back in, shifting in his seat until he finds a position in which his thong isn’t bothering him.


	3. III

Dean was 28 the first time he bought himself some makeup of his own: a tube of mascara from the dollar store. He strategically placed it on the counter under the chips, pens, and instant coffee. He knew that cashiers don’t actually care what people buy, but he couldn’t help measuring the girl’s reaction when she scanned the offending item. Dean thought he saw her raise an eyebrow but he never was quite sure.

Now, at 37, Dean expertly applies mascara to his lashes, blinking and eyeing himself in the bathroom mirror. He finishes off this look with a clear lip gloss, smacking his lips with a satisfying pop. He steps back and marvels at how good he looks like this. The gold eye shadow accentuates his green eyes, the black eyeliner adds a seductive air, and the light dusting of blush makes him look softer, creates a feminine glow about him. He stands in front of the mirror for a few more moments then wets a washcloth with makeup remover. He sighs as he wipes away all his hard work, rinsing the cloth then tossing it into the hamper when he’s finished. He places his makeup back into his shaving case and exits the bathroom, passing Sam on the way to his bedroom.


	4. IV

Dean wishes he were like Sam. Sam has that easy, confident masculinity that doesn’t need to be forced. Sam brushes off quips about his long hair, about the way he eats (“trying to watch your girlish figure, Samantha?”) Dean has always felt the need to assert his masculinity: the car he drives, the clothes he wears, the music he listens to, the food he eats, the beer he drinks—the list could go on for days. He always needs to prove to people that he is a man’s man and not the “queer” that he really is.

The first time a girl called him pretty, Dean was 14 years old. John had the family hunkered down in some small Iowa town and Dean attended the local high school for a whopping four months. In that time he’d gotten to know the girl he sat beside in physical science well enough that she even asked him to the homecoming dance. He didn’t respond right away. He’d initially felt a rush of inadequacy. Wasn’t it supposed to be the guy who asked the girl to the dance? But then he’d realized that that was stupid and thought about how much courage it must have taken her to ask him, and he said yes.

A couple hours into the dance and Dean and Linda were sat on the steps in front of the school. It was a chilly night and Linda leaned in close to Dean. He wrapped his arms around her tightly and smiled, pleased with himself, when she sighed contentedly. He paled when she turned her face towards his and whispered, “You’re so pretty, Dean.”  
He froze, then hauled himself up from the steps, giving her an excuse about his dad expecting him home right about now. That night he’d begged John to leave, telling him that the school’s guidance counselor had begun asking questions. They left the next morning.

He never saw Linda again.

The second time it happened Dean handled it better. Rhonda Hurley was a kinky broad, Dean had to hand it to her. She knew what she liked and what she liked was men in women’s lingerie. At first he had protested but the more he looked at the pink satin panties the stronger the urge grew in his belly and he finally gave in. 

Rhonda stood him in front of her mirror and called him pretty while she stroked him through the material and Dean couldn’t help but agree.

Dean has never really seen himself as “pretty”. Handsome sure. His face is symmetrical, his physique is toned and muscular, he’s tall… But the things about him that make him handsome, also make him masculine. When Rhonda called him pretty he had believed it in the heat of the moment. But once Rhonda had fallen asleep Dean had slipped out of her apartment without so much as a goodbye. As he walked back to the motel he’d thought about that word. Pretty. “You look pretty like that, Dean.” He wanted to believe it, and in fact he had…until he came and Rhonda told him to take off the panties before he stretched them out too much. Then he was faced with reality. He wasn’t pretty all the time, only when he dressed like a woman. But he couldn’t dress like a woman. Imagine the look on John’s face if Dean came home wearing a dress. Imagine fighting off ghouls in heels. Yeah, right. He couldn’t shake the feeling though. That was the first time he’d ever felt comfortable in his own skin. That was the first time he’d ever felt…right.


	5. V

Dean doesn’t keep his pink disposable razor in the shower like women do. Instead he keeps it in his shaving kit, which he carries with him to the bathroom whenever his balls are beginning to itch. Sam doesn’t think that’s weird… right? What’s weird about a man taking his shaving kit to the bathroom? 

Like most people, Sam leaves his kit in the bathroom. Dean wouldn’t dare. There’s too much risk in that. Even if he left it in a drawer, Sam might run out of shaving cream and need to borrow some of his. Dean can just see the look on his brother’s face when he unzips the leather pouch and finds the pink razor, not to mention the makeup. 

He shakes his head. It’s not good for him to think about that for too long—makes him anxious. And Lord knows he doesn’t need more anxiety. He steps into the shower, razor and raspberry shaving cream in hand, and revels in the hot water on his back. He wets his hair then steps away from the spray to lather the saving cream over his pubic hair.

The first time he tried this he was 17 and he’d used John’s electric razor and it hadn’t ended well. It was five years before he tried it again and he’d been smarter that time. Now it’s a regular thing, part of his routine as much as shaving his face is.

It’s nice. A little feminine secret that feels amazing under silk or lace panties, something that makes him feel pretty without anyone ever knowing his perverted secret.


	6. VI

When Kyle Watterson first offered him a cigarette Dean turned it down. He liked Kyle; they were friends—and Dean didn’t exactly have a lot of those at Middlebrook High. But although John Winchester may not have won any Parent of the Year awards, he had taught his sons not to smoke.

Kyle played basketball, went to church dutifully every Sunday, and had good grades and a steady, cute girlfriend. He was everything Dean wasn’t. Kyle smoked, yes, and Dean figured that was about his only flaw. Kyle was an all-around nice guy. He was also the type to pick up strays, which is how he and Dean became friends, after Dean swaggered into senior algebra with his cocky attitude on display. Some asshole tripped him on his way to his seat and Dean had to practically bite his tongue in half as he continued on to his seat in the back row. He slumped down into the chair, arms crossed, head held high as the other kids laughed along with that asshole. Kyle, sitting next to him, was the only person who didn’t. He saw through Dean’s façade and said quietly to him, “Hey, fuck that guy. He’s failing just about every class and probably won’t even graduate on time.”

Dean was surprised. People didn’t usually treat him… nicely. He eyed the nice-guy and breathed a laugh.

The guy smiled. “I’m Kyle.”

“Dean.”

They didn’t speak again for the remainder of class.

Later that day Dean found himself in the cafeteria, wandering slowly around the room, looking for a place to sit. Every table was full and he couldn’t just sit down with a group of strangers who would inevitably find a reason to dislike him. Sam didn’t have lunch until next period and anyway, he would probably already have some dweeby friends to sit with. So Dean wandered, alone.

“Dean!”

He glanced around, unsure where the call came from.

“Dean!”

It was Kyle, waving him over to a table by the window. Dean smiled in relief as he walked over to Kyle and his two other friends.

Two months later and Dean would actually call Kyle his best friend, after Sam.  


The second time Kyle offered him a cigarette Dean hesitated before he turned it down. Kyle smiled and shrugged. “Good boy, Dean.”

Those words sat with Dean for days afterword. John used to say that to him when he was a kid and it had always filled him with pride. Kyle said it almost as a joke, a dare. But not quite. Dean couldn’t figure out why it agitated him so much, but it did.

A week later when Kyle jokingly offered him a cigarette for the third time, Dean accepted.

He didn’t expect to like the taste—and he didn’t at first. However, he didn’t choke and sputter like so many people do when they take their first drag.

He pulled the cigarette away from his lips and examined it as he exhaled. Pall Mall Menthols.

He took another drag, then another. The mint tasted nice and the smoke filled his lungs, warming him. It was certainly something he could see himself getting used to.

Kyle laughed, “I’m a bad influence on you.”  


After the basketball team won the regional championship, Kyle and his friends threw a party at his house to celebrate. Dean was not the party type, but he went, reluctantly, at Kyle’s request. Dean took his time flirting with a few girls while Kyle made the rounds, making sure everyone had a good time and didn't break anything. When two of his teammates showed up with a keg Kyle pulled Dean out onto the back porch, where only a few other people were milling around.

Dean was out of his element at this party and was a bit antsy as a result. He knew that Kyle didn’t really like drinking but Dean rubbed his sweaty palms on his jeans and gestured toward the house.

“You mind if I get a drink?”

A sympathetic smile appeared on Kyle’s lips. “Go ahead, Dean. Have a good time.”

“I’ll be right back!” Dean called, already hurrying inside.

Alcohol has always made Dean feel better and allow him let down his walls and have fun, and after a few drinks he was actually having a genuinely good time.

When he and Kyle ended up on the back porch again, this time alone, Dean had begun to slur his words and was hanging lightly onto his friend. He clumsily pulled his cigarettes and lighter out of his pocket and stuck one in Kyle’s mouth and lit it, then did the same for himself.

They sat in silence for a little while, both lost in thought with the cool night air and the sounds of the party inside settling between them.

“Do you ever wish you were someone else?” Kyle asked suddenly.

“Huh?” Dean looked at him quizzically, thrown off guard by the question.

“Yeah, you know…do you ever wish you weren’t… you?”

Dean chewed his lip, the alcohol making it hard for him to think. “I guess so, yeah.”

“It’s like, I know I’m lucky to have the life I do, but… I can’t help but wonder what it would be like to just wake up one day as somebody else.”

They fell back into silence, both thinking about another possible life until Dean admitted softly, “I wish I were a woman.”

Kyle’s head whirled around to face him. “What?”

“Yeah…”

“Are you serious?”

The alcohol in his system did not permit Dean to think about his words before they left his mouth. “Like, I see all these women wearing makeup and shit and I just… I wish I could do that. I wish I were like them. Pretty, you know? And soft—“

“Dean, what the fuck?”

Dean paled, Kyle’s obvious disgust sobering him instantly. He had completely misread the situation. Kyle probably meant _I wonder what it’s like to be poor, or black, or a senator._ Not _I wish I could wear lipstick and nylon stockings out in public._

He couldn’t say anything. Even if he weren’t drunk he didn’t think he’d be able to smooth talk his way out of this one. So he remained silent and stared off into the distance, waiting for Kyle to say something.

Kyle didn’t say anything for a while either. Dean could hear him shifting in his chair but he didn’t chance a glance in his direction.

After a few more moments Kyle stood and said, without making eye contact, “I’m going to see what everyone’s up to,” and hurried back into the house.

Dean nodded and waited until he heard the backdoor close before he got up and left out the side gate.

On his walk to the bus stop Dean lit up a cigarette and thought about Kyle and how fucking stupid he had been to admit that shit. He had never told anyone about wanting to be a woman and had just lost his only friend because of it. Kyle was probably inside telling the whole school about what a freak Dean was. He was probably using words like “queer”, “faggot”, and “pervert”. He had made the mistake of trusting someone with his secret and would never do that again.

He wiped away a tear and exhaled smoke into the cool night air.

He dropped out of high school the following Monday and a week later John whisked them away to another town, to another hunt.


	7. VII

The black eye that Sam is sporting is new and nasty, with no plans on going away any time soon. Unfortunately, Sam’s driver’s license expires in two days.

“Dean?” Sam questions quietly as Dean opens the bag of cosmetic sponges and pulls out a fresh one. The tone is eerily similar to the one he used when they were kids and didn’t want to upset his older brother by asking too many questions.

“Shut up.”

Sam does.

Dean grits his teeth and refuses to look at Sam as he pours the liquid concealer onto the sponge. His face is on fire and he knows there's no hiding his embarrassment from Sam.

“Look up,” Dean orders. Sam complies silently and allows his brother to dab the makeup onto his bruised skin.


	8. VIII

He saw the way they looked at him. There was no mistaking it. They glanced at the bag dangling delicately from his strong shoulder, then up at his face. He couldn’t describe their reactions if he wanted to, wouldn’t even know the right words to use. It was like a combination of fascination, disgust, curiosity, and a million other things all rolled into one reactionary face. He rubbed his right palm on his jeans then used the hand to grasp the door handle and haul it open.

He was momentarily overwhelmed by the thumping music, the swooping, dancing lights, and the mass of bodies moving against one another on the dance floor. As he looked around slowly to take it all in (and to locate the bar) he had trouble distinguishing at first who exactly was male and who was female. There were men in drag, women in dresses and heels, men in jeans and dress shirts, women in the same, and various other forms of dress. Each person seemed to truly own the style they were wearing though, and no one looked out of place. Not even Dean.

The smile creeping over his lips felt foreign, but so deserved.

He found the bar, ordered a vodka sunrise, and leaned back on the bar to watch the swirl of colors around him.

“I like your purse,” a voice appeared in his ear.

Startled, Dean turned to his right to see a man in full, fabulous drag leaning into his personal space. She smelled like lavender.

“Thanks,” he replied, a blush creeping onto his cheeks.

She reached out a jeweled hand and gently fingered the strap hanging from his shoulder.

“What’s your name?” She asked.

“Dean,” he replied.

“I’m Summer, Dean. Nice to meet you.” She offered her hand for him to kiss. He did and, when she smiled, felt proud of himself for properly understanding the gesture. 

“Is this your first time at the Horse of a Different Color?”

“Yeah. I’m uh, not from around here.” He rubbed a hand on the back of his neck and grinned sheepishly. “Is it that obvious?”

Summer winked. “Yes. But that’s not a bad thing.”

They chatted for a while. Summer, citing that she needed a break from the festivities, perched on a bar stool, slipped out her heels, and rubbed unabashedly at her sore feet.

As Dean felt their conversation coming to its natural close, he worked up the courage to ask the question he had been wondering since he first walked into the club that night.

“How do you do it?”

“What’s that, baby?” She turned her gaze back toward him from where it had wandered to the dance floor.

“How do you do it?” She raised her eyebrows, silently asking for more to go on. “You know, how do you find the courage to…” he motioned to her outfit, makeup, and hair, a gesture that swept her from head to toe.

She looked back to the dance floor and for a moment Dean thought she was going to completely ignore the question. Maybe he had offended her…

She looked at him again, a furrow between her brows and a tight frown on her lips.“Dean, sweetie. The question isn’t how do I have the courage to do this,” she mimicked Dean’s gesture on herself. “The question is how do I have the courage to be Mike from IT five days a week? This is who I really am. This doesn’t take courage at all. Suffering takes courage, baby. And when I wear those slacks and that button up… well, it takes courage for me not to come in to the office in full drag and show those motherfuckers who’s boss.”

Dean smiled.

“And I am the boss. Literally! I’m the goddamn manager! But if I showed up to work like this, you better believe my ass would be out of a job in no time flat. Hmm…”

“So why do you do it then? Work in IT and slacks?” He asked.

She grinned slyly at him and rolled her eyes. “Honey, I may be good but I ain’t that good. Drag ain’t payin’ no bills!”

Dean laughed and Summer joined him. She slipped her heels back on, then stood and reached to her purse to pay for her drink. Dean put a hand out. “I’ve got it.”

She smiled again and thanked him. “You’re a real nice person Dean; I can sense that from more than just you payin’ for my drink.” She paused for a moment and eyed him. She leaned in to speak in his ear and fingered his purse strap again. “You deserve to feel good.”

She turned away with a wave—just a waggle of the painted fingers on her left hand—and walked out into the sea of bodies on the dance floor.

Dean watched her until she completely disappeared, then turned back to the bar and reached into his purse to pay for their drinks.


	9. IX

Sam can’t cook so Dean does it. He also enjoys it, if he’s being honest. It’s an activity with a positive reward, something he can put time and effort into and enjoy the result. He’s never thought of it as a feminine activity, never as a domestic activity, he just does it. He’s the cook in their household, his and Sam’s. He’s always been cooking for Sam, since they were just kids. Back then it used to be hot dogs and fried bologna sandwiches, but just last night he made beef wellington. Sam looked like he had died and gone to Heaven and that made Dean very happy.

He went to the local used book store and picked up a couple cook books a while back and they all have dog-eared pages and bookmarks sticking out of them now. He’s tried a lot of the recipes they contain and some have been misses but most have been hits.

“You’ve got a knack for this, I’m telling you,” Sam said to him one evening with a mouth full of chicken Alfredo (the Alfredo sauce made from scratch).

He used to be into porn where women were bent over the kitchen counter wearing nothing but aprons, being fucked by their husbands. He’s still into that, it’s just not his “thing” at the moment.

Would it be nice to be fucked like that? By a man, in the kitchen, in an apron? Or by a woman…? In his mind’s picture, he’s definitely the one bent over the counter, wearing an apron, getting fucked. As to who’s doing the fucking, he’s not sure. He guesses it would be a man, because of the scenario, the position, but really it doesn’t have to be.

Is he bisexual?

The thought comes as a surprise, although he knows it shouldn’t. He’s only ever slept with women but he’s always thought about men too.

Why hasn’t he had sex with a man before? He should try it, shouldn’t he? To be sure…

Hmm, he thinks as he stirs the cheddar broccoli soup on the stove. He’s pretty sure that he’s sure he’s bisexual. Not that being sure changes anything. He’s still Dean who smokes menthols and wears thongs. He still wears makeup when no one else can see it. He still likes to cook and watch Westerns and drink top shelf whiskey. He still shaves his legs.

He salts the soup then brings the wooden spoon to his mouth for a taste.

Perfect.


	10. X

Dean is not a shorts kind of guy. It’s got to be beyond hot for him to even think about donning a pair.

Today is sweltering. 102, his weather app says is the heat index.

He hadn’t planned on going anywhere today, so he’d put on the only pair of shorts he owns: cut off jean shorts that sit just above the knee. He didn’t buy them like that—he actually cut the legs off of an old, well-worn pair of light wash blue jeans he’s owned since Sam was at Stanford. And damn, are they comfortable. 

Sam doesn’t let him smoke in the bunker (“it’s not good for the books”) so he hauls his ass up from his armchair and goes outside. He’s standing outside the front entrance of the bunker when he hears Baby’s engine. Sam pulls up and parks near where Dean is standing.

He gets out and Dean can see through the thin plastic grocery bag that there’s ice cream in there. 

Sam stops and eyeballs his shorts. “I haven’t seen those in a long time.”

Dean chuckles and flicks his cigarette butt onto the ground. Only then does he remember his shaven legs.

He watches Sam’s back as he walks into the bunker and wonders if Sam noticed. If he did, did he think anything of it? Of course he would have to think it was strange, right? His brother with shaven legs, that’s so very unlike Dean, at least the way he presents himself to the world. Dean doesn’t think that Sam has seen his legs since the last time he wore these shorts. How long ago was that? A few years, probably.

But… that’s not right is it? Just a few months ago Sam helped him clean up a wound just below his right knee that he’d acquired on a hunt. He’s been shaving for years and Sam was actually touching his leg for an extended period of time. There’s no way he didn’t notice…

And there has to have been times when his sleep pants bunched up when he was lazing around the bunker. And at motels they change in front of each other—it isn’t practical not to. Surely Sam would’ve noticed on one of those many, many occasions. 

“You coming?”

He blinks to where Sam is holding the door open for him and follows his brother inside. Sam takes his bags to the kitchen and puts the groceries away, leaving the mint chocolate chip ice cream out on the table.

“You want some?” Sam asks.

“Uh, yeah, sure.”

“Get the bowls, would you?”

Dean pulls two bowls down from the cupboard while Sam fishes in a drawer for the ice cream scooper. Dean lays them out and watches Sam’s face as he scoops out a slightly larger portion for Dean, then one for himself.

“Thanks,” he mumbles and seats himself at the table. Sam follows suit.

While they eat Sam chatters about what he bought. He got what Dean asked him to but not the name brand that he put on the list because the generic is way cheaper and tastes ex—

“Why haven’t you ever said anything about me shaving my legs?”

Sam’s mouth is still open so he closes it at Dean’s outburst and studies his older brother for a moment. Dean holds his breath.

“I don’t know,” is what he replies.

“What do you mean, you don’t know?”

Sam takes another bite of his ice cream and, with his mouth full, says, “It’s just never seemed like a big deal.” He scoops up the melted puddle at the bottom of the bowl and pauses with the spoon half way to his mouth. “Is it?”

Yes! “No.”

“I didn’t think so.” Sam slurps up the ice cream then gets up and puts his bowl in the sink. “I mean, swimmers shave their legs, right? It’s not weird.”

“I don’t swim.”

Sam sighs and turns around to face him. “Is there something you need to tell me, Dean?”

This is it. This is the moment Dean has been picturing in his head for years. The picture in his head is actually strikingly similar to how it’s playing out in real life: in the kitchen, over a meal, after sharing some minute yet extremely personal detail about himself. There have been many versions of Sam in his head, some understanding, some accusatory, some upset, some happy. He’s still not sure which version will be the real one yet.

He looks down at the nearly empty bowel in front of him. “No.”

Sam’s brow furrows. “Are you sure?”

He can’t look up. It’s going to be Ridicule Sam, he can feel it.

“Dean, come on,” Sam sits back down across from him. “It’s obvious you want to say something.”

“It’s…” he scrubs his face with his hands. “You’re not gonna like it.”

Sam snorts. “That’s never stopped you before.”

“It’s… I’m…” He realizes as he searches for the courage to tell his baby brother, that he’s never actually thought about how to put his feelings into words before.

“Spit it out,” Sam tells him.

“Would you just shut up for a minute?” Dean snaps and the amusement falls from Sam’s face like a scolded child.

Dean’s mouth opens and closes a few times before he begins, “Since I can remember, I’ve never felt… right.”

“How do you mean?”

He bites his lip and thinks. “In my own body, I mean… Or maybe I don’t mean it like that…”

Sam listens silently, a look of slight concern adorning his features.

“Like, I’m a man, right? But am I really? I have a dick, yeah, and that’s fine. I don’t mind my dick. I enjoy having it, you know? Hah…” he chuckles awkwardly. “But there’s always been something missing. I think,” he pauses, sighs. “I think I don’t really feel right as a man…” he says finally, letting it hang in the air between him and Sam.

“Oh,” Sam utters quietly and looks down at his folded hands on the table for a moment, then back up at Dean. Sam’s gaze is focused intensely on him. “Okay.”

Dean lets out a heavy sigh. “Okay?”

Sam clears his throat and runs a hand through his hair before he starts talking. “Yeah, okay. I mean, you’re still Dean. I just, I don’t know what to say. I still love you.”

“Really?” Dean asks, surprised.

“Are you serious? Of course. We’ve literally died for each other, Dean. We’ve gone to Hell and back for each other. You think this would make me, what, hate you? I could never.”

Dean can’t speak or else he might start bawling. 

“So…” Sam goes on, ever the curious one, “are you gay?”

The question startles Dean. “What?”

“I’m sorry, I shouldn’t have assumed.”

Dean sucks in a breath and tries to formulate a response but Sam speaks again.

“It’s just that, I mean, I’ve noticed how you look at guys sometimes. Not that I care. You’re just a pretty sexual person, you know. And we drink a lot, and you’re looser when you drink, because who isn’t right? And um, you, I’ve noticed you… I don’t know if ‘check out’ would be the proper term—“

“Sam,” Dean halts Sam’s nervous babble.

“Sorry,” he mutters.

Dean sighs again and Sam just can’t seem to control himself. “Are you a lesbian?”

“Jesus, Sam!”

“What?! I thought that was a valid question!”

Dean has to agree that, yes it is a valid question but he isn’t sure of the answer.

“Honestly? I don’t know.” He rubs the heel of his palms into his eyes. He blinks and looks at Sam who’s waiting patiently for whatever answer Dean’s willing to give him.

“I like having a man’s body, for the most part. I can’t imagine what it would be like not to have a dick. Well okay, I can, but I don’t think I want that. So to answer your question, no, I’m not a lesbian; I’m bisexual.”

Upon saying to out loud to another person for the first time, Dean realizes that this is in fact the truth. No more thinking that he might be bisexual, he knows for sure that he definitely is.

Sam nods and looks at his hands again.

“Look, I don’t know if I have all the answers you want, because I probably don’t know some of them myself. But you can ask. I’ll try my best to make you understand, okay?”

Sam smiles sympathetically and nods. “Thank you for telling me. I know that couldn’t’ve been easy. And yeah, I will ask. I just need some time to get used to the idea. But I will! You don't have to worry about that.”

Well, at least that's one thing he doesn't have to worry about anymore.


	11. XI

Dean once had sex with a woman he’d met at a gay bar. Why either of them was there, he never understood. She was straight and he hadn’t been looking to take anyone home. But she found him sitting alone at the bar and plopped down on the open stool next to him.

When it came out that he wasn’t gay she jumped at the opportunity and they ended up back at her apartment after Dean had paid for a few of her drinks with bills he’d fished out of his purse. She questioned it of course, and he shrugged off the scrutiny. “It matches my outfit,” (which it most certainly did not).

She took off her shirt and pants as soon as the door to her apartment closed behind them. She helped Dean off with his jacket and shirt then began unbuckling his belt. He pulled her hands away and made a show of it himself, revealing, to her immense delight, the red lace panties underneath.

She treated his cock like it was a clit. Not even Rhonda had done that. But she didn’t say anything about it; never called it a clit, dick, cock, or anything else. It was all in how she handled it. She rubbed the head with just her thumb through the panties while Dean mouthed at her neck. She took it in her ass like the goddamn anal queen and called him “baby” all the while.

She offered to let him stay the night but he politely refused and got dressed while she started the shower.

“Sure you don’t want to join me, sweetie?”

The way she said that, “sweetie,” genuinely made him shiver. She didn’t say it in ridicule or sarcastically. She didn’t say it with lust in her voice, but the way she said it was nice. It felt genuine.

She must’ve known the way he was, how he truly felt about himself.

He still thinks about that night occasionally. What if he had stayed and hopped in the shower with her? What if he’d asked for her number, or hell, her last name?

What if they’d made a life together? Could she have accepted this part of him? Could anybody?


	12. XII

**Notes for the Chapter:**

> A follow-up to chapter 9. I felt like it needed a little more something to bring that story point home.   
> Also, I apologize to all Floridians. I actually side with Sam on this one! :D

He can tell that Sam is trying and really, that’s all Dean can ask for. He hadn’t thought that Sam would accept him at all, so this good, great, excellent.

But…

It’s not like he didn’t notice the look on Sam’s face at the Laundromat in Springfield when he threw a few pairs of panties into the machine with the rest of their darks. The look was gone before Dean met Sam’s eyes but they both knew that Dean had in fact seen it.

Dean might not go so far as to call it disgust… discomfort maybe?

Knowing about Dean’s gender… _thing_ , whatever it is, he’s still not sure what to call it—is different than actually seeing it he supposes.

And he gets that, he really does. He knows that it must be weird for Sam to see Dean doing feminine things after his 38 years of brutal masculinity. But if it were Sam’s sister’s panties in the washer it would be no problem.

Then later, at their motel room, Dean left his shave kit out on the bathroom counter like he never would have dared before. Sam was in there brushing his teeth with the door open and Dean needed his comb and hair gel. He brushed shoulders with Sam in the small space and unzipped his case.

In the mirror, Dean could see Sam turn his head slightly to catch a glimpse of the contents inside. Dean retrieved his items and quickly zipped it shut then shuffled out past Sam, shave kit in hand.

It was a lot more of that kind of thing until they completed the hunt and returned home.

At the Bunker they each have plenty of space to be away from one another and do their own thing. Dean figures it’s a lot easier for Sam to ignore his confession there than it is on hunts. Trapped in the close confines of motel rooms they see everything the other does. Dean can’t count the number of times he’s watched Sam blow his nose then examine the tissue afterwards. It doesn’t get any less gross over time.

Will his panties seem less gross to Sam over time?

 

Their next hunt leads them to Tallahassee in August.

“I fucking hate Florida,” he grumbles as they cross the state line.

“Why?” Sam asks.

Dean looks over like he can’t believe Sam would even question that.

“Because Florida is America’s wang. That makes Texas the ball sack. You know where we are right now? Florida’s panhandle. You know what that is, Sammy? America’s sweaty taint!”

“Florida is a beautiful state, Dean.”

Dean scoffs, “In December maybe. Right now it’s a sweaty taint.”

Sam shakes his head, “Try not to say that to any of the locals, if you could.”

“Are you telling me that your taint doesn’t turn into a fucking swamp in August? Because mine sure as hell is!”

“You’re an idiot. And disgusting.”

Dean grins in spite of himself. “Let’s just get this case wrapped up as soon as possible.”

 

“I’m not staying here.”

Sam throws him a bitch face. “You’ll be fine; it’s just for one night and then we’ll be back on the road in the morning.”

“It’s too goddamn hot for the A/C in this dump to be busted. We’re going somewhere else.”

“You know we’re tight on funds at the moment and we’ve already paid for ‘this dump,’ so we’re not going anywhere. We had a good hunt today, just focus on that,” Sam declares finally and slumps back against the headboard, arms crossed over his middle.

Dean shoves the duffel he was trying to repack off his bed angrily.

“Relax, okay? Just open the window and once the sun sets all the way it will cool off.”

Sam’s right, it does cool off, but only marginally. Dean checks the temperature from his phone. 88 degrees. And that didn’t even begin to touch the humidity. How Sam can sleep in this he has no clue. Dean threw off the blankets and top sheet in frustration over an hour ago, and then his shirt followed soon after. As he tosses and turns his sleep pants stick to his legs, and the sheet underneath him is just damp enough to piss him off even more.

He looks at Sam’s form in the darkness. The man hasn’t moved a muscle since he fell asleep almost two hours ago. Dean silently climbs out of bed and pulls off his pants. He then lies in bed for a while, nervously contemplating Sam’s reaction if he wakes up before him in the morning.

They’re just black, he tells himself. Black satin briefs with only a tiny bow on the front, that’s it. He’d put on boxer briefs instead but they’re, well, downright disgusting at this point.

Sans pants and covers, Dean is finally able to fall asleep in just under fifteen minutes.

When he wakes the next morning, still tired even though he slept longer than he had intended, Sam is gone and so is the Impala. Dean remembers his inner turmoil from last night and panics. Did Sam leave because he couldn’t bear to see Dean’s sick desire in the flesh? He comes away from the window and steps into the bathroom.

While waiting for the shower to heat up he stares at himself in the mirror. Sam wouldn’t just take the car and leave him stranded here over a pair of underwear, he reasons with himself, no matter how disgusting it is. Sam had put up with it thus far, anyway. And they live under the same roof so certainly this would be a situation he’d want to avoid.

Still, the worry creeps around Dean’s mind as he steps under the spray. After they wrapped up their hunt yesterday he silently promised himself a nice slow jerk off session in the shower today, the only place he had any privacy from his brother. Now he is too nervous about the meaning of Sam’s disappearance to even look at his pelvis.

Sam probably thought it was a gross sex thing, his choice of panties. That couldn’t be further from the truth. Sure, maybe for some of his partners it was, but never for Dean. They made him feel as normal as boxers probably felt for Sam. If kinky women liked it then who was he to judge? It had made for some damn good nights, that’s for sure.

Dean doesn’t enjoy feeling like a sexual deviant around his brother, though. As he towels dry only does the sound of his stomach growling make his thoughts turn to something else. He comes out of the bathroom and performs a sniff test to find the least filthy pair of underwear (the same panties as last night). Just as he’s buttoning up his jeans the door opens and Sam walks in, donned in his jogging clothes with sweat dripping off of him.

“Hey,” he says as he throws the keys onto the table.

Dean gapes at him then remembers himself and closes his mouth before Sam can see.

He clears his throat. “Where were you?” he asks from inside a t-shirt as he slides it over his head.

“Running. There was this cool trail I saw on Trip Advisor so I figured that was better than the side of the road like usual.”

Dean nods, feeling foolish.

“How’d you sleep last night?” Sam asks as he pulls his damp shirt over his head and drops it at the foot of his bed.

“Uh, shitty… shittily?” Dean wonders if that’s a real word. “You get the picture.”

Sam smiles. “Yeah, I noticed that by the state of you this morning,” he chuckles, then heads into the bathroom where the door closes behind him with the click of the lock.

Dean stares at the off-white door. What the hell did that mean? The way Sam had said it sounded light, jovial even. But he mentioned it, so that had to be a hint, right? Sam’s way of telling Dean that he didn’t want to wake up to that sight ever again, to never be in a situation where he’d have to witness Dean’s offending behavior.

When Sam emerges from the bathroom Dean is perched on the edge of the bed. He watches Sam dress, politely averting his eyes until Sam has his underwear on.

Sam says absently, “We need to hit a laundromat on our way out of town today. I’m out of clean—“

“Sam,” Dean says lowly.

His brother looks at him for the first time since his shower. His arms are suspended in the air, frozen as he attempts to fold a pair of dirty jeans. It would be comical, the way the pants continue to sway back and forth after Sam shook them out, that being the only movement between them. Dean gulps and looks Sam in the eye, mustering all the courage he has to say, “Do you think I’m disgusting?”

Sam just blinks at him for a moment then folds the jeans and drops them unceremoniously into his duffel. He sits on the edge of the bed across from Dean, clearly picking up the fact that this is about to be a serious conversation.

“What?”

“I see the way you look at me. Last time, when we were doing laundry in Illinois, you looked at...at my,” he struggles to say the word, “panties,” he sighs, “like, like I was some freak. And I’m just sorry that I told you about this, about me. It’s my dirty secret and you should never have had to know about it.” Dean sighs again around the lump in his throat. “I can understand why you think I’m disgusting and I should’ve just kept it to myself. Nobody wants to know that their bother is some kind of pervert—”

“Dean,” Sam pushes in.

Dean’s mouth hangs open on the words he was about to ramble on with. Sam runs a hand through his own wet hair.

“I don’t think any of that,” he nearly whispers.

Dean says nothing, waiting, frightened, too nervous that Sam will explain that he actually feels worse.

“I’ll admit, I was shocked when you first told me. But not because I think you’re a freak.”

Dean winces at the word, even though he had just said it himself. Hearing it come out of Sam’s mouth after imagining it doing so for so long was still a shock to Dean’s system, regardless of its context.

“It’s just, I’ve always seen you as this man’s man, you know. But when you told me, it was like so many things about you that I’d never even noticed suddenly clicked into place. And the more I think about, the more it makes sense.”

Dean raises a brow at that.

“I mean, it’s never been a secret to me that you’re insecure—“

“I am not!”

Sam ignores his outburst. “—But I never knew why. Now I know. And, just understanding that part of you makes the rest of you make sense too. That probably sounds dumb. I’ve just been surprised over and over again, ever since you told me, about just how much you were hiding. I see your…underwear and it makes me think about how long you’ve had to hide that. And the fact that you thought you _had_ to hide it, hide who you are, that just, I don’t know. It’s sad.”

Dean inhales to respond but Sam cuts him off.

“I’m not saying that I pity you, that’s not at all what I’m saying here.” Sam pauses to find the right words. “It… it makes my heart hurt to know that you’ve felt ashamed for so long, when you have nothing to be ashamed of.”

Dean looks at his hands in his lap, then back up at Sam, and once again at his hands. He simultaneously wants to cry and hug his smart, wonderful, amazing little brother. Instead he whispers, “Thank you.” He clears his throat. “It’s just that Dad never would’ve been so understanding.”

“I’m not Dad,” Sam declares, “and I’m never going to be. So don’t feel like you have to hide from me. I’m just adjusting to it, you know? I never had the slightest clue about…how you really are, and now I’m getting so much at once that, yeah, it surprises me. I can’t lie, it’s weird. But it’s weird now and then it won’t be. It’s like… if you told me, ‘Hey Sam, I love kale.’ Even that would take a moment or two to process.” He smiles. “You told me about your _gender_. That is so much more important.” He shakes his head. “I’m sorry if I’ve made it seem like I felt any way other than accepting. You’re still my big brother. Or, well…”

Dean scrubs his face and feels himself smile for the first time that morning.

“Shut up, bitch.”

Sam laughs out loud. Dean shakes his head, stands, and looks around the room. He spots his duffel where he left it.

“Well Dean, your _panties_ are fucking rank, so if you don’t mind could we please go wash these clothes now?”

Dean laughs and Sam looks visibly relieved.

“Just, not in Florida, though. Jesus I can’t be in this state another minute.”

“As long as you keep the windows down, that’s fine by me.”


	13. Chapter 13

**Notes for the Chapter:**

> As we all know, Dean has a lot of demons, some of them a lot harder to deal with than his gender and sexuality.

To Dean, some of the little things can be a lot.

He’s a big tough man—John made sure to drill that into him from an early age, which is why the idea is so difficult to escape.

Those “little things” are usually small occurrences that to everyone else would seem meaningless. A hand on his back in a crowded bar as a young lady passes behind him. Sausages hanging from a meat hook in a Polish deli. Dogs growling…

It’s things that remind him of Hell. Memories that he thought he had moved past—or at least shoved down deep enough that they didn’t haunt him on a daily basis. He could actually sleep peacefully now, all these years later.

One of the reasons he got on so well with Benny in Purgatory is because Benny had demons too. Not the same ones, but plenty just as bad.

There was the time in Purgatory when a particularly nasty creature came at them silently from behind. It grabbed Dean in a chokehold and whispered into his ear, “Allistair says hello,” before Benny lunged forward and ripped its throat out with his bare hands. 

It didn’t matter that the monster was full of shit that it had most likely overheard gossiped in dark shadows, it still left Dean frozen in his tracks. His hunter instincts drained, just like the piss that ran down his legs as the creature fell to the ground behind him. 

He had never pegged Benny for a hugger, but the vampire took him into both arms, never mind the urine or the blood an Benny’s hands.

Benny never asked what it had said and Dean never told him, but it wasn’t the last time they had found a small comfort in one another down there.

But back topside he didn’t have a Benny to lean on, no questions asked. No one—save Sam—could ever begin to understand the trauma he’d lived through in Hell. Talking about it to Sam only became a therapy session and he didn’t want that. Nor did he want to risk reopening any of Sam’s delicately sutured Hell wounds either. So he shoved it deeper and tried not to let the little things get to him too badly.

 

It was an accident that he found the support group. He saw it while having his morning coffee and reading yesterday’s newspaper that Sam had forgotten to toss in the recycling bin. Dean had already scanned the obits and weather, searching for anything out of the ordinary, when he glanced over the personals. An ad for _Trauma Survivors and PTSD Support Group_ caught his eye. The caption read, “Talk with people who understand. Tuesday evenings, Bethel Church, 7pm” and an address.

He didn’t bother to tell Sam about it, just ripped the ad out, shoved it into his robe pocket, and waited for Tuesday. 

When the night finally came he put on his favorite pair of comfortable, orange silk briefs under his worn old blue jeans, for the reminder that he would be okay even if this didn’t work out. To Sam, he lied and said he was going out for a few beers.

He sat in the church parking lot until 6:58, drumming his hands on the steering wheel and debating on whether or not to bolt. He compromised with himself and got out, reasoning that he didn’t have to talk if it didn’t feel right. No one could make him.

The group he found milling about in a classroom was not the one he expected to find. The desks were pushed to the walls and a circle of folding chairs took their place in the center of the room. He honestly thought, he realized with a pang of guilt, that he’d be entering a room of depressed and dejected, weak and fragile looking ex-soldiers, more than a few with missing limbs or other disfigurements. 

That was not at all the case. It was actually quite a diverse group of people. A lot more women than he expected, for one. There were some scrawnier men, yes, but there were a few burlier men too. Some older men and women, some quite young—early 20s. Only one man looked the way Dean had been expecting; obviously a veteran if the Desert Storm cap told him anything. He was probably late forties, early fifties and sat in a wheelchair, missing one leg above the knee. What caught Dean the most off-guard about the whole situation, though, was that people were laughing and joking. Smiling, catching up on each other’s week since the last meeting.

“Come on in, buddy!” A hand waved Dean away from the door where he had been hovering.

“Is this the… support group?” He asked dumbly, not sure what else to say.

“Sure is. Name’s Matt,” he gripped Dean’s hand firmly and shook it enthusiastically. He gestured to his left. “This here’s Mary and Paul.”

“Dean.”

“Glad you could make it, Dean,” Matt smiled, as if he’d always been expecting him. He looked down at his watch then announced to the room, “Okay folks, it’s seven-oh-five, we should go ahead and get started.”

Everyone took a chair in the circle, Dean being one of the last to sit. He ended up next to Mary with Desert Storm on his right.

Matt facilitated. “I’m glad to see you all back here tonight. I hope everyone’s had a good week. As you can see, we have a new face joining us,” he gestured to Dean. “Why don’t you go ahead and introduce yourself?”

He cleared his throat nervously and raised a hand with what felt like a grimace be he hoped didn’t appear that way. “I’m Dean. I uh, I’ve never been to one of these things before so… uh…” The hand ended up on the back of his neck, kneading the muscles nervously.

Matt took over, “Welcome Dean. We’re all just here to talk and listen. It just helps to be around people who know how you’re feeling and what you’ve been through. We all do; no one’s here to judge.”

Dean relaxed a little. “Mary, why don’t you start us out.” She spoke without interruption about how she’d been coping the past week, what things she’d overcome and what she still needed to work on. Then they went around the circle after that, conveniently so that Dean would be last. Some people shared memories of their experiences, some just talked about each day that had passed, like each was its own battle. As Desert Storm—Jerry—concluded, Matt gestured to Dean. “Is there anything you want to talk about tonight? If not that’s absolutely fine.”

He thought about it for a moment. He knew that the broad details of what he said would have to be lies. He couldn’t exactly tell these people that he’d spent forty years in Hell, but he wanted to be as honest as possible, otherwise what would be the point?

He rubbed his sweaty palms on his jeans and thought about his orange silk. He handled coming out (although he didn’t really like that terminology) to Sam, he could handle this too.

“I was a marine,” he chose carefully, after listening to everyone’s stories and learning that there were no marines in the room. He had passed as one before to other vets; he figured it was a safe choice here. “A damn good one too,” he smiled which earned a hushed chuckle from the room. “I was captured and…tortured for information. For a really long time. They promised me that it would get better if I told them what they wanted. I uh, held out for as long as I could but… I just couldn’t take it anymore... And it did get better, it really did. But I know that what I did cost other people a lot. That it hurt so many people. Eventually I was rescued… but if I had just held out longer then all those people wouldn’t have been hurt, would still be alive… I just wasn’t strong enough.”

Silence followed, broken a few moments later by Matt. “If you weren’t strong enough then you wouldn’t be sitting here right now. Hell, you might not even be alive right now. I think most of us can only begin to imagine what you experienced, and that we surely don’t want to. But we all know strength when we see it. The fact that you can even talk about it is more than most could do.”

Jerry spoke, “I’ve seen more than enough good men turn to some dark shit ‘cause of the things they’ve seen. Drink, drugs, violence, you name it. What happened ain’t your fault. I know you don’t believe that now but it’s the truth.”

Matt nodded. “That’s why we’re all here. To overcome darkness.”

“And it’s a helluva lot cheaper than booze,” a woman piped up from across the circle, and the room erupted in laughter.

Matt waved his hands. “Alright settle down, folks,” he smiled, shaking his head. “Well, I guess we’ll call that a night, then. See you all next week!”

As people filed to the back of the room for doughnuts and coffee several of them came up to Dean and wished him well, hoped to see him next week.

“You will,” he promised and meant it.


End file.
